炔基三氟硼酸盐作为有机合成中的通用工具：合成螺缩酮的新途径。
Alkynyltrifluoroborates as versatile tools in organic synthesis: a new route to spiroketals.
作者信息
Doubský Jan, Streinz Ludvík, Saman David, Zedník Jirí, Koutek Bohumír
机构信息
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic.
出版信息
Org Lett. 2004 Dec 23;6(26):4909-11. doi: 10.1021/ol047987k.
PMID:15606097
Abstract
[reaction: see text] A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.
摘要
[反应：见正文] 描述了一种简单有效的合成螺环缩酮的两步法。关键步骤包括通过内酯与炔基三氟硼酸钾的开环反应制备官能化的羟基α-炔基酮，随后对螺环缩酮前体中间体进行钯催化的氢化/螺环化反应。
相似文献
1
Alkynyltrifluoroborates as versatile tools in organic synthesis: a new route to spiroketals.
Org Lett. 2004 Dec 23;6(26):4909-11. doi: 10.1021/ol047987k.
2
Allyl sulfones as precursors to allylzincs in the palladium-catalyzed zinc-ene cyclization: highly efficient synthesis of enantiopure (-)-erythrodiene.
Org Lett. 2005 Aug 18;7(17):3637-40. doi: 10.1021/ol051049i.
3
Synthesis of spirocyclic C-arylribosides via cyclotrimerization.
Org Lett. 2006 Aug 3;8(16):3565-8. doi: 10.1021/ol061350e.
4
An efficient synthesis of highly functionalized [5,6] aromatic spiroketals by hetero-Diels-Alder reaction.
Org Lett. 2008 Mar 6;10(5):721-4. doi: 10.1021/ol7029068. Epub 2008 Feb 12.
5
Unified, radical-based approach for the synthesis of spiroketals.
Org Lett. 2007 Apr 26;9(9):1773-6. doi: 10.1021/ol070488+. Epub 2007 Mar 29.
6
Au-catalyzed cyclization of monopropargylic triols: an expedient synthesis of monounsaturated spiroketals.
Org Lett. 2009 Jan 1;11(1):121-4. doi: 10.1021/ol802491m.
7
Domino Pd-catalyzed Heck cyclization and bismuth-catalyzed hydroamination: formal synthesis of elacomine and isoelacomine.
Chemistry. 2011 Jan 10;17(2):626-33. doi: 10.1002/chem.201002287. Epub 2010 Nov 16.
8
A highly efficient access to spiroketals, mono-unsaturated spiroketals, and furans: Hg(II)-catalyzed cyclization of alkyne diols and triols.
Org Lett. 2011 Jun 17;13(12):3178-81. doi: 10.1021/ol201102x. Epub 2011 May 23.
9
Stereoselective spirolactam synthesis via palladium catalyzed arylative allene carbocyclization cascades.
Org Lett. 2010 Sep 3;12(17):3784-7. doi: 10.1021/ol101425y.
10
2,6-Diazaspiro[3.3]heptanes: synthesis and application in Pd-catalyzed aryl amination reactions.
Org Lett. 2008 Aug 21;10(16):3525-6. doi: 10.1021/ol801293f. Epub 2008 Jul 17.
引用本文的文献
1
Evidence that Cerambycid Beetles Mimic Vespid Wasps in Odor as well as Appearance.
J Chem Ecol. 2017 Jan;43(1):75-83. doi: 10.1007/s10886-016-0800-1. Epub 2016 Dec 19.
2
Preparation of the 5/5-spiroketal of the ritterazines.
J Org Chem. 2007 Apr 27;72(9):3454-7. doi: 10.1021/jo0626461. Epub 2007 Mar 31.
Zotero 插件